Cyclades Islands

White cuboid houses with blue frames on a hill above the endless azure is what most people would think as an image of a Greek island. That image usually derives from the Cyclades islands, a large group of diverse islands that consist of many different cultures and landscapes. The Cyclades offer visitors the choice to experience the famous, the fashionable, the crazy, the historic, the sophisticated, the quiet, the exotic and the beautiful.

There are plenty of sailing routes for a traveler depending on the desired combination of Cycladic features while each route can provide short travelling times between islands and a breathtaking sailing experience.


Santorini and Mykonos

Santorini and Mykonos form the touristic heart of Cyclades, each fulfilling the Greek island image but in a particularly unique way. Considering that Mykonos and Santorini are much visited and crowded, it is very likely that the possibility of docking or mooring cannot be guaranteed. In addition, Santorini has a docking area too far from any place of interest.

However, if you would like to spend some time in either of these islands in addition to other amazing Greek Islands, Trip to Sail can arrange a package for a day or a few nights in Mykonos or Santorini at the beginning/conclusion of your sailing trip. Package can include a ferry or flight and accommodation.

Defining the trip
There are plenty of amazing sailing itineraries for Cycladic islands, depending on the starting/ending charter base, the season, the overall duration of the sailing trip and what characteristics the traveler seeks from it. Moreover, the mixed factor of the weather (such as Greek Meltemi winds) is very likely to alter a route any time during the trip. In any case, your Trip-To-Sail representative will guide you in advance so that by the time of your departure, you and your skipper will choose a convenient and comfortable route to more than enough ideal sailing destinations.  Embarkation points for Cyclades could be Lavrio, Alimos, Paros and Syros.
Some tips
We suggest to keep a daily schedule with short sailing distances and mostly follow an off the beaten track route. Also, give a definetely worthwhile time to the inland of the islands.
Because of the possibility of rough seas, we are only able to offer these routes from Athens weather permitting. Your captain will have an accurate forecast when you arrive and will make the final decision. Safety is our number one consideration.

Starting Point: Athens (Alimos)

Finishing Point: Athens (Alimos)

Possible Visiting Places/Islands: Kythnos, Serifos, Sifnos, Kea, Sounio,  Kalamaki

Visit all the shades of blue while sailing from Athens to the islands and back. Explore the time passed by visiting the Acropolis of Sifnos, the prehistoric settlement of Agia Irini in Kea, The throne of Cyclops in Serifos and the Mesolithic cottage of Marulas in Kythnos. The local architecture combined with the scenic settlements and harbors award the visitor with a timeless sight. Guide yourself in the city’s path and explore the ceramic oven in Sifnos, the lighthouse of Kea, the tiny chapels and the quite beaches.

Starting Point: Athens (Lavrio)

Finishing Point: Athens (Lavrio)

Possible Visiting Places/Islands: Kea, Kythnos, Serifos, Sifnos, Syros, Andros, Tinos, Mykonos, Paros, Antiparos, Naxos.

Starting from the ancient remains of Delos, Andros and the Portara in Naxos, moving to the famous visiting landscapes of Little Venice of Mykonos or the windmills, each island adds value and attraction on visitors trip.  Discover natural beauty while taking a tour or walk on Antiparos’ or Kythnos’ caves, the river of Andros, the hot-springs of Serifos and the multifarious bays. For art lovers the museums in Andros, Kea and Tinos can be a great amusement. Spend a relaxed afternoon visiting a castle in Naxos, horseback riding in Kea or a wine taste in Andros.

Starting Point: Paros

Finishing Point: Paros

Possible Visiting Places/Islands: Paros, Antiparos, Naxos, Ano Koufonisi, Amorgos, Ios, Folegandros, Keros, Schoinousa, Donoussa, Irakleia, Syros, Mykonos, Sifnos, Serifos, Kimolos, Milos, Tinos, Andros, Kythnos, Kea

Some of the most visiting islands of Greece are included in these sailing route options if you reach Paros by a charter flight.. With the sun to be on its peak of temperature and long-lasting hours, the islands of Cyclades offer a sally of any taste. Deepening on the weather sailors can choose either an intense or lax route in consultation with the skipper. Big caves, lots of castles, hand-painted churches, small pavements and ancient finds offer a complete experience to the visitors. Do not forget to donkey ride, to get a spring bath in Milos, to visit Skiadi in Kimolos and to explore the under-water world in Ios.

Starting Point: Syros

Finishing Point: Syros

Possible Visiting Places/Islands: Paros, Antiparos, Naxos,  Syros, Mykonos, Sifnos, Serifos,  Tinos, Andros, Kythnos, Kea

Cyclades were named after the Greek word “circle” due to their geographic order. The complex provides a beautiful combination of beaches, sights, ancient ruins and nature. The diversity entertainment varies on each island beginning with taverns and local live amusement parties and finishing with unceasing partying. Big caves, lots of castles, hand-painted churches, small pavements and ancient finds are some of the sights musts visited. Do not forget to visit Portara in Paros, the caves in Andros, the dovecotes in Tinos, the windmills in Mykonos, Despotiko in Antiparos and the paths of Syros.


Despite its tricky approach, Vlichada at the south end of Santorini could be the only mooring option of the island where you can be safe from storms or leave the yacht unattended. However, Vlichada marina is full of local daily charters and it is unlikely for a visitor to find any mooring space available. Last but not least, main town is on the opposite side of the island, so you would need at least 45 minutes taxi ride to get in any place of interest.

Take a flight or ferry to this amazing island with a Trip-To-Sail package in addition to your sailing trip.

Search for the lost City of Antlanits while wandering in the rocky paths and the ston-paved alleys. Discover all the colours of the island, volcano black-sand or red-sand beaches, golden sand or gravel seasides and deep-blue bays. Santorini is one of the most famous destination in the world to meet romance and love in the time of sunset, with a great view at the red-blue Aegean sea.


Due to its popularity, Mykonos is one of the most visiting sailing destination for tourists that leads to a huge traffic on the available marinas. Moreoverer, the marina is full of local daily charters and it is unlikely for a visitor to find any mooring space. For all the above we suggest to take a flight or ferry to this amazing island with a Trip-To-Sail package in addition to your sailing trip.

There are many international and Greek brands’ shops available for shopping. Night life covers all the desires and needs, from a local brewery up to an erratic clubbing till the morning. Add some spice on your time in the island to have some fun with watersports or driving in the island’s narrow streets.